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Dudley Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Dudley vacation rentals

Interior

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is AED 463
AED 715 total
includes taxes & fees
14 Aug - 15 Aug
The Tree House at Underhill Hollow
Exterior

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is AED 463
AED 694 total
includes taxes & fees
23 Aug - 24 Aug
Wizard's Roost at Underhill Hollow
Property grounds

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 694 total
includes taxes & fees
17 Aug - 18 Aug
SteamPunk Bunk House and Intergalactic Way Station
Interior

4. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is AED 184
AED 488 total
includes taxes & fees
13 Aug - 14 Aug
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
1 bedroom, internet, bed sheets

5. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
The price is AED 294
AED 421 total
includes taxes & fees
16 Aug - 17 Aug
Clean & Cozy Private room - 3 floor_R 1
Exterior

6. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (6 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is AED 483
AED 858 total
includes taxes & fees
10 Sep - 11 Sep
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior

7. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (34 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is AED 645
AED 957 total
includes taxes & fees
17 Aug - 18 Aug
Dove Cabin up in the Trees
Interior

8. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very Good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is AED 217
AED 324 total
includes taxes & fees
14 Aug - 15 Aug
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Exterior

9. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The Carriage House at Chaprae Hall
Interior

10. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is AED 775
AED 1,461 total
includes taxes & fees
4 Sep - 5 Sep
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Exterior detail

11. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
The price is AED 900
AED 1,163 total
includes taxes & fees
15 Aug - 16 Aug
Cozy 1-bedroom cottage in serene Pomfret.
Property grounds

12. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is AED 585
AED 744 total
includes taxes & fees
17 Aug - 18 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Smart TV

13. Serenity meets Taradise

Serenity meets Taradise
Union
The price is AED 397
AED 635 total
includes taxes & fees
15 Aug - 16 Aug
Serenity meets Taradise
Terrace/patio

14. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.8 out of 10, Exceptional, (46 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
The price is AED 477
AED 1,206 total
includes taxes & fees
11 Sep - 12 Sep
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

15. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AED 757
AED 873 total
includes taxes & fees
13 Aug - 14 Aug
Cottage by the Castle – Downtown Spencer
Dining

16. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AED 1,836
AED 2,967 total
includes taxes & fees
1 Sep - 2 Sep
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Property grounds

17. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is AED 345
AED 922 total
includes taxes & fees
1 Sep - 2 Sep
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Smart TV

18. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is AED 524
AED 1,407 total
includes taxes & fees
13 Aug - 14 Aug
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Interior

19. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
10.0 out of 10, Exceptional, (1 review)
The price is AED 662
AED 1,493 total
includes taxes & fees
3 Sep - 4 Sep
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Living area

20. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is AED 251
AED 372 total
includes taxes & fees
13 Aug - 14 Aug
Clean & Cozy Private- 3 floor_R 4
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dudley Hotel Reviews

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

10/10 Excellent
"N/A"
Renata 1-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Sturbridge by IHG

Frequently asked questions

Are there vacation rentals in Dudley?

Yes, there are vacation rentals in Dudley near TriState Speedway, or you can go with a secluded option if you want a relaxing stay. Dudley is known for its restaurants.

What's the top vacation rental that Dudley has to offer?

Home Away from Home!: Visitors like this Dudley vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

How many vacation rentals are there in Dudley?

Choose from 3 Expedia vacation rentals in Dudley for a memorable vacation.

What’s there to see and do in Dudley?

Stevens Park and Berthol Field are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include TriState Speedway. Dudley Hill Golf Club at Nichols College and Conant Library are other places to visit while you're in town.

What’s a vacation rental in Dudley like?

Vacation rentals are private properties you can book for a long or short time in Dudley. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.